Solution-processable triazole-based polymers and methods of making the same

Abstract

Disclosed herein are polymers comprising at least one alkyne functional group, at least one azide functional group, and a conformational bend outside of coplanarity of 30 or greater. Also disclosed herein are methods of making and using the same.

What is claimed is: 
     
       1. A polymer, comprising:
 at least one azide functional group; 
 at least one alkyne functional group; and 
 a spirocenter,
 wherein the polymer is obtained from (i) a first monomer having at least a first azide functional group and (ii) a second monomer having at least a first alkyne functional group, and 
 wherein at least one monomer of the first and second monomers has a conformational bend in which one or more bonds connecting the at least one monomer to one or more additional monomers in a monomer chain are 30 degrees or greater away from co-planarity. 
 
 
     
     
       2. The polymer of  claim 1 , wherein the polymer has a degree of polymerization of 30 or greater based on the number-average degree of polymerization. 
     
     
       3. The polymer of  claim 1 , wherein the polymer has a molecular weight of 60,000 g/mol or greater based on the weight average molecular weights for the polymer. 
     
     
       4. The polymer of  claim 1 , wherein the polymer has a polydispersity index of 1 or greater. 
     
     
       5. The polymer of  claim 1 , wherein the polymer has a solubility of 20 mg/mL or greater in common organic solvents, and wherein the common organic solvents comprise one or more of acetaldehyde, acetic acid, acetone, acetonitrile, butanediol, butoxyethanol, butyric acid, diethanolamine, diethylenetriamine, dimethyl acetamide (DMAc), dimethylformamide (DMF), dimethoxy ethane, dimethyl sulfoxide (DMSO), dioxane, ethanol, ethylamine, ethylene glycol, formic acid, furfuryl alcohol, glycerol, methanol, methyl diethanolamine, methyl isocyanide, N-methyl-2-pyrrolidone (NMP), propanol, propanediol, propanoic acid, propylene glycol, pyridine, tetrahydrofuran (THF), triethylene glycol, dimethyl hydrazine, hydrazine, hydrofluoric acid, hydrogen peroxide, nitric acid, sulfuric acid, pentane, cyclopentane, hexane, cyclohexane, benzene, toluene, chloroform, diethyl ether, and dichloromethane. 
     
     
       6. The polymer of  claim 1 , wherein the polymer further comprises:
 monomers comprising:
 at least two azide functional groups; and 
 at least two alkyne functional groups, and 
 
 wherein the polymer comprises a polytriazole. 
 
     
     
       7. The polymer of  claim 1 , wherein the polymer comprises two or more spirocenters. 
     
     
       8. The polymer of  claim 1 , further comprising one or more of an alkane group, an ester functional group, a halide functional group, a cycloalkane functional group, an aromatic functional group, an amide functional group, a heterocyclic functional group, a thioester functional group, an imide functional group, a carbamate functional group, and a carbonate functional group.